Kylie Jenner Then & Now: See Photos of the Makeup Mogul’s Unbelievable Transformation

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August 10, 2023 1:28PM EDT
Kylie Jenner then and now
Jason Sean Weiss/BFA.com/Shutterstock

Kylie Jenner was just a kid when ‘Keeping Up With The Kardashians’ started, so it’s almost impossible to believe the youngest sister, born Aug. 10, 1997 is now 26. Since she’s become the head of a top makeup brand and welcomed two kids. Her looks have also made quite the transformation over the years. Long gone are the days of dainty lips and a pale complexion. Now Kylie tends to mirror her older sisters’ styles, embracing that big pout, deep tan, and bombshell curves, as you can see in this then/now photo here. From early events to becoming a business big shot, Kylie has practically grown up in front of our eyes. Now, we’re taking a look back at her wild transformation. To see more images of Kylie through the years, check out the rest of the gallery!

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Kylie Jenner: Then & Now

Kylie Jenner: Then & Now
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Kylie Jenner was just a kid when ‘Keeping Up With The Kardashians’ started, so it’s almos impossible to believe the youngest sister, born Aug. 10, 1997 is now 25. Since she’s become the head of a top makeup brand and welcomed two kids. Her looks have also made quite the transformation over the years.

Long gone are the days of dainty lips and a pale complexion. Now Kylie tends to mirror her older sisters’ styles, embracing that big pout, deep tan, and bombshell curves, as you can see in this then/now photo here.

From early events to becoming a business big shot, Kylie has practically grown up in front of our eyes. Now, we’re taking a look back at her wild transformation. To see more images of Kylie through the years, check out the rest of the gallery!

August 9, 2022, 3:11PM
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Kylie Jenner At The Taste Of Beverly Hills Food & Wine Festival

Kylie Jenner At The Taste Of Beverly Hills Food & Wine Festival
Picture Perfect/Shutterstock

Kylie Jenner attends the Taste of Beverly Hills Food and Wine Festival on Sept. 2, 2010. She looked super cute in this gray and black mini-dress.

April 27, 2020, 10:20AM
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Kylie Jenner At The Premiere Of ‘After Earth’

Kylie Jenner At The Premiere Of ‘After Earth’
Kristin Callahan/Shutterstock

Kylie Jenner attends the ‘After Earth’ film premiere on May 29, 2013. She looked great in this little black ensemble.

April 27, 2020, 10:20AM
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Kylie Jenner At The 2014 Billboard Music Awards

Kylie Jenner At The 2014 Billboard Music Awards
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Kylie Jenner attends the 2014 Billboard Music Awards arrivals on May 18, 2014. She rocked turquoise dyed hair. 

April 27, 2020, 10:20AM
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Kylie Jenner At The American Music Awards in 2014

Kylie Jenner At The American Music Awards in 2014
Stewart Cook/Shutterstock

Kylie Jenner attends the American Music Awards on Nov. 23, 2014. She wore Alexandre Vauthier and looked stunning. 

April 27, 2020, 10:20AM
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Kylie Jenner At The 2015 Billboard Music Awards

Kylie Jenner At The 2015 Billboard Music Awards
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Kylie Jenner at the Billboard Music Awards arrivals on May 17, 2015. She wore this belted dress and looked so fierce.

April 27, 2020, 10:20AM
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Kylie Jenner At The Launch Of Kendall & Kylie Collection

Kylie Jenner At The Launch Of Kendall & Kylie Collection
Matt Baron/BEI/Shutterstock

Kylie Jenner attends the Kendall and Kylie Collection launch at Topshop on June 30, 2015. She wore Topshop and High-Street.

April 27, 2020, 10:20AM
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Kylie Jenner At The 2015 ESPY Awards

Kylie Jenner At The 2015 ESPY Awards
Matt Baron/BEI/Shutterstock

Kylie Jenner attends The ESPY Awards on July 15, 2015. She stunned in this gorgeous gold dress.

April 27, 2020, 10:20AM
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Kylie Jenner At The 2015 VMAs

Kylie Jenner At The 2015 VMAs
Jim Smeal/Shutterstock

Kylie Jenner at the MTV Video Music Awards on Aug. 30, 2015. She wore Balmain and looked stunning this gold ensemble.

April 27, 2020, 10:20AM
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Kylie Jenner Sits Front Row At Prabal Gurung

Kylie Jenner Sits Front Row At Prabal Gurung
Steve Eichner/WWD/Shutterstock

Kylie Jenner in the front row of the Prabal Gurung show during New York Fashion Week on Sept. 13, 2015. She wore Prabal Gurung.

April 27, 2020, 10:20AM
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Kylie Jenner At The Opening Of Sugar Factory American Brasserie

Kylie Jenner At The Opening Of Sugar Factory American Brasserie
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Kylie Jenner attends the Sugar Factory American Brasserie Grand Opening on Sept. 16, 2015. She was the host of the event.

April 27, 2020, 10:20AM
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Kylie Jenner at Cosmopolitan Magazine’s 50th Birthday Celebration

Kylie Jenner at Cosmopolitan Magazine’s 50th Birthday Celebration
Matt Baron/Shutterstock

Kylie Jenner at Cosmopolitan Magazine’s 50th Birthday Celebration on Oct. 12, 2015. She wore white and worked a blonde hairdo. 

April 27, 2020, 10:20AM
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Kylie Jenner At The Launch Of The Balmain x H&M Collection

Kylie Jenner At The Launch Of The Balmain x H&M Collection
Patrick Lewis/Starpix/Shuttersto

Kylie Jenner attends Balmain x H&M Collection Launch in New York on Oct. 20, 2015. She looked so regal in her detailed dress.

April 27, 2020, 10:20AM
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Kylie Jenner At The 2015 American Music Awards

Kylie Jenner At The 2015 American Music Awards
Matt Baron/Shutterstock

Kylie Jenner at the American Music Awards on Nov. 22, 2015. She wore Bryan Hearns and looked so good in this leather dress. 

April 27, 2020, 10:20AM
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Kylie Jenner With Green Hair

Kylie Jenner With Green Hair
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Kylie Jenner out and about in Los Angeles on Nov. 30, 2015. She was seen leaving the DASH store.

April 27, 2020, 10:20AM
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Kylie Jenner At Rihanna’s Diamond Ball

Kylie Jenner At Rihanna’s Diamond Ball
Matt Baron/Shutterstock

Kylie Jenner attends Rihanna’s Diamond Ball on Dec. 10, 2015. She wore August Getty. 

April 27, 2020, 10:20AM
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Kylie Jenner At The InStyle & Warner Bros Golden Globe Party

Kylie Jenner At The InStyle & Warner Bros Golden Globe Party
Matt Baron/Shutterstock

Kylie Jenner attends the InStyle And Warner Bros Golden Globe Party Jan. 10, 2016. She looked angelic in her gorgeous champagne dress. 

April 27, 2020, 10:20AM
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Kylie Jenner At The 2016 Met Gala

Kylie Jenner At The 2016 Met Gala
David Fisher/Shutterstock

Kylie Jenner at The Metropolitan Museum of Art’s Costume Institue Benefit Celebrating the Opening of Manus x Machina: Fashion in an Age of Technology on May 2, 2016. She wore Balmain and glimmered from head to toe. 

April 27, 2020, 10:20AM
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Kylie Jenner At A 2016 Pretty Little Thing Launch Party

Kylie Jenner At A 2016 Pretty Little Thing Launch Party
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Kylie Jenner at the PrettyLittleThing.com US Launch Party on July 7, 2016. She wore Pretty Little Thing for the event. 

April 27, 2020, 10:20AM
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Kylie Jenner At The Marie Claire Image Maker Awards

Kylie Jenner At The Marie Claire Image Maker Awards
Matt Baron/Shutterstock

Kylie Jenner attends the Marie Claire Image Maker Awards on Jan. 10, 2017. She wore Balmain and looked like a vision in purple.

April 27, 2020, 10:20AM
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Kylie Jenner At The 2017 Met Gala

Kylie Jenner At The 2017 Met Gala
Shutterstock

Kylie Jenner attends The Costume Institute Benefit celebrating the opening of Rei Kawakubo/Comme des Garcons: Art of the In-Between at The Metropolitan Museum of Art on May 1, 2017. She wore Atelier Versace and looked so stunning with her blonde bob. 

April 27, 2020, 10:20AM
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Kylie Jenner At The 2018 Met Gala

Kylie Jenner At The 2018 Met Gala
Nina Westervelt/BEI/Shutterstock

Kylie Jenner attends The Metropolitan Museum of Art’s Costume Institute Benefit celebrating the opening of Heavenly Bodies: Fashion and the Catholic Imagination on May 7, 2018. Kylie stunned in her Alexander Wang ensemble. 

April 27, 2020, 10:20AM
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Kylie Jenner At The 2019 MTV VMAs

Kylie Jenner At The 2019 MTV VMAs
Kristina Bumphrey/StarPix/Shutte

Kylie Jenner at the MTV Video Music Awards on August 20, 2019. She wore Tom Ford with shoes by Olgana Paris. 

April 27, 2020, 10:20AM
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Kylie Jenner At The 2019 Met Gala

Kylie Jenner At The 2019 Met Gala
Matt Baron/Shutterstock

Kylie Jenner attends the Costume Institute Benefit celebrating the opening of Camp: Notes on Fashion at The Metropolitan Museum of Art on May 6, 2019. She wore Atelier Versace and looked so stunning in her lavender look. 

April 27, 2020, 10:20AM
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Kylie Jenner, Stormi Webster, & Travis Scott At The Premiere Of ‘Travis Scott: Look Mom I Can Fly

Kylie Jenner, Stormi Webster, & Travis Scott At The Premiere Of ‘Travis Scott: Look Mom I Can Fly
Broadimage/Shutterstock

Travis Scott, Stormi Webster, and Kylie Jenner attend the ‘Travis Scott: Look Mom I Can Fly’ film premiere on August 27, 2019. It was a family affair for the trio.

April 27, 2020, 10:20AM
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Kylie Jenner At The 2020 Vanity Fair Oscars Party

Kylie Jenner At The 2020 Vanity Fair Oscars Party
Matt Baron/Shutterstock

Kylie Jenner attends the Vanity Fair Oscar Party on Feb. 9, 2020. She wore Ralph and Russo and looked truly stunning. 

April 27, 2020, 10:20AM
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Kylie Jenner & Family At The Parsons 2021 Benefit

Kylie Jenner & Family At The Parsons 2021 Benefit
Andy Kropa/Invision/AP/Shutterst

Happy family. Travis Scott, Stormi Webster and Kylie Jenner attend the 72nd annual Parsons Benefit presented by The New School at The Rooftop at Pier 17, in New York on Jun. 15, 2021.

April 12, 2022, 4:41PM
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Kylie Jenner Leaves Carbone

Kylie Jenner Leaves Carbone
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Pregnant Kylie Jenner seen leaving Carbone Restaurant, during New York Fashion Week. Her white dress and long coat were so chic.

April 12, 2022, 4:41PM
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Kylie Jenner In 2022

Kylie Jenner In 2022
Shutterstock

White hot! Kylie carries a Cinderella-style glass purse during an LA outing.

April 7, 2022, 8:57AM
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Kylie Jenner In 2022

Kylie Jenner In 2022
TheRealSPW / MEGA

Revving engines. Kylie Jenner goes ‘Biker Chic’ in a one piece leather outfit and Fox Motocross gloves after leaving dinner with Mom Kris Jenner and Sister Khloe Kardashian in Hollywood on Apr. 5, 2022.

April 12, 2022, 4:41PM
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Kylie Jenner At The Premiere Of ‘The Kardashians’

Kylie Jenner At The Premiere Of ‘The Kardashians’
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Strike a pose. Kylie Jenner looks stunning as she quietly attended The Kardashian’ Hulu TV show viewing party in Hollywood on Apr. 8, 2022. It was her first major appearance since welcoming her son.

April 12, 2022, 4:41PM
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Kylie Jenner at Mugler Couturissime Exhibition

Kylie Jenner at Mugler Couturissime Exhibition
Gregory Pace/Shutterstock

Kylie Jenner slayed in this skintight strapless black corset gown with a bedazzled headpiece at the Mugler Couturissime Exhibition Opening in New York on Nov. 5, 2022.

August 10, 2023, 1:16PM
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Kylie Jenner at Schiaparelli show

Kylie Jenner at Schiaparelli show
David Fisher/Shutterstock

Kylie Jenner wore this massive lion head on a black velvet dress at the Schiaparelli show during Paris Haute Couture Fashion Week on January 23, 2023.

August 10, 2023, 1:16PM
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Kylie Jenner at Jean Paul Gaultier show

Kylie Jenner at Jean Paul Gaultier show
Laurent VU/SIPA/Shutterstock

Kylie Jenner rocked this cutout blue & black gown to the Jean Paul Gaultier show during Paris Haute Couture Fashion Week on January 25, 2023.

August 10, 2023, 1:16PM
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Kylie Jenner at Vanity Fair Oscar Party, 2023

Kylie Jenner at Vanity Fair Oscar Party, 2023
Anthony Harvey/Shutterstock

Kylie Jenner wore this metallic black & silver Maison Margiela to the Vanity Fair Oscar Party in Los Angeles on March 12, 2023.

August 10, 2023, 1:16PM
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Kylie Jenner at the 2023 Met Gala

Kylie Jenner at the 2023 Met Gala
David Fisher/Shutterstock

Kylie Jenner showed off her toned leg in this cutout red dress at The Metropolitan Museum of Art’s Costume Institute Benefit celebrating the opening of the ‘Karl Lagerfeld: A Line of Beauty’ in New York on May 1, 2023.

August 10, 2023, 1:11PM
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Kylie Jenner at Mugler H&M Los Angeles Celebration

Kylie Jenner at Mugler H&M Los Angeles Celebration
Jason Sean Weiss/BFA.com/Shutter

Kylie Jenner donned this oversized black leather trench coat with sheer black tights & black heels at the Mugler H&M Los Angeles Celebration on May 10, 2023.

August 10, 2023, 1:16PM